1,3‐Bis(2‐thienylmethylene)1‐1H,3H1‐thieno[3,4‐c]thiophene: A Precursor for a New Low Band Gap Polymer

Michael Hanack*, Ulrich Schmid, Ursula Röhrig, Jean‐Marc ‐M Toussaint, Christine Adant, Jean‐Luc ‐L Brédas

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1H,3H1‐thieno‐[3,4‐c]thiophene(9), for polyarenemethylenes (PAM), which are predicted to be low band gap polymers, is obtained by a Knoevenagel‐type condensation of 1H,3H1‐thieno[3,4‐c]thiophene 2‐oxide (7) with 2‐thiophenecarbaldehyde followed by reduction of the intermediate sulfoxide 8 with 2‐chloro‐1,3,2‐benzodioxaphosphole. Several investigations with cyclic voltammetry and UV‐Vis‐NIR spectroelectrochemistry (SEC) are carried out on 9. The experimental data are compared with the results of electronic band structure calculated on the basis of an MNDO‐optimized geometric structure by VEH pseudopotential method.

Original languageEnglish (US)
Pages (from-to)1487-1491
Number of pages5
JournalChemische Berichte
Issue number6
StatePublished - Jun 1993


  • 1H,3H1‐Thieno[3,4‐c]thiophene derivative
  • Polyarenemethylenes
  • Polymers, low band gap

ASJC Scopus subject areas

  • General Chemistry


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